Basic Info

Common NameO-Toluidine(F05289)
2D Structure
Description

The chemical properties of the toluidines are quite similar to those of aniline and toluidines have properties in common with other aromatic amines. Due to the amino group bonded to the aromatic ring, the toluidines are weakly basic. None of the toluidines is very soluble in pure water, but will become soluble if the aqueous solution is acidic due to formation of ammonium salts, as usual for organic amines. At room temperature and pressure, ortho- and meta-toluidines are viscous liquids, but para-toluidine is a flaky solid. This can be explained by the fact that the p-toluidine molecules are more symmetrical and fit into a crystalline structure more easily. p-Toluidine can be obtained from reduction of p-nitrotoluene. p-Toluidine reacts with formaldehyde to form Troger's base.

FRCD IDF05289
CAS Number95-53-4
PubChem CID7242
FormulaC7H9N
IUPAC Name

2-methylaniline

InChI Key

RNVCVTLRINQCPJ-UHFFFAOYSA-N

InChI

InChI=1S/C7H9N/c1-6-4-2-3-5-7(6)8/h2-5H,8H2,1H3

Canonical SMILES

CC1=CC=CC=C1N

Isomeric SMILES

CC1=CC=CC=C1N

WikipediaO-Toluidine
Synonyms
        
            2-AMINOTOLUENE
        
            o-Toluidine
        
            2-Methylaniline
        
            95-53-4
        
            2-Toluidine
        
            o-Tolylamine
        
            2-Methylbenzenamine
        
            ortho-toluidine
        
            o-Methylaniline
        
            Benzenamine, 2-methyl-
        
Classifies
                

                  
                    Pollutant
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassToluenes
Intermediate Tree NodesNot available
Direct ParentAminotoluenes
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsAminotoluene - Aniline or substituted anilines - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Amine - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as aminotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and one amino group.

Properties

Property NameProperty Value
Molecular Weight107.156
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Complexity70.8
Monoisotopic Mass107.073
Exact Mass107.073
XLogP1.3
Formal Charge0
Heavy Atom Count8
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9625
Human Intestinal AbsorptionHIA+0.9906
Caco-2 PermeabilityCaco2+0.8599
P-glycoprotein SubstrateNon-substrate0.8504
P-glycoprotein InhibitorNon-inhibitor0.9541
Non-inhibitor0.9869
Renal Organic Cation TransporterNon-inhibitor0.8785
Distribution
Subcellular localizationLysosome0.7562
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7992
CYP450 2D6 SubstrateNon-substrate0.8614
CYP450 3A4 SubstrateNon-substrate0.7676
CYP450 1A2 InhibitorInhibitor0.6284
CYP450 2C9 InhibitorNon-inhibitor0.8051
CYP450 2D6 InhibitorNon-inhibitor0.9406
CYP450 2C19 InhibitorNon-inhibitor0.7568
CYP450 3A4 InhibitorNon-inhibitor0.9445
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6737
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9514
Non-inhibitor0.9344
AMES ToxicityAMES toxic0.8875
CarcinogensNon-carcinogens0.5479
Fish ToxicityHigh FHMT0.6676
Tetrahymena Pyriformis ToxicityHigh TPT0.8900
Honey Bee ToxicityLow HBT0.7032
BiodegradationNot ready biodegradable0.7073
Acute Oral ToxicityIII0.7892
Carcinogenicity (Three-class)Non-required0.7094

Model Value Unit
Absorption
Aqueous solubility-0.9127LogS
Caco-2 Permeability1.7144LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1987LD50, mol/kg
Fish Toxicity2.0744pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.2570pIGC50, ug/L

References

TitleJournalDatePubmed ID
Determination of primary aromatic amines in cold water extract of coloured paper napkin samples by liquid chromatography-tandem mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2016 Jun27146949
Modulation of antioxidant defence system by dietary fat in rats intoxicated with o-toluidine.Hum Exp Toxicol2002 Dec12540036

Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]